In April 1985, Jim Crockett Promotions and Championship Wrestling from Georgia essentially merged. Anderson was teaming with Thunderbolt Patterson in GCW just as Marty Lunde was debuting in JCP as Arn Anderson. It seemed like a natural fit to put the two "Andersons" together, especially considering their extremely similar facial appearance. Anderson soon turned on Thunderbolt and teamed with Arn as the Minnesota Wrecking Crew.[3]

Anderson returned to wrestling with WCW in 1989 to reform the Four Horsemen with Flair, Arn and Sting.[4] They quickly kicked Sting out of the group, and Anderson retired again to manage the Horsemen, who by then also included Barry Windham and Sid Vicious.[4] By 1990, Anderson had been chosen to head the booking committee for WCW, which was at that time beginning to phase out the use of the NWA name on its television programming. Appearing in the credits for WCW pay-per-views (PPVs) under his real name, Anderson was responsible for some of the more infamous creative ideas tried by WCW. Among his creations were The Black Scorpion, which was intended to be a nemesis from Sting's past.[5] After several miscues, the Scorpion's identity was eventually revealed as Ric Flair, in a ploy to confuse Sting and force him to lose the WCW World Heavyweight Championship.[5] Around 1991, Anderson became a referee. After Bill Watts was ousted, Anderson took control of WCW.

When Eric Bischoff took over control of WCW in 1993, both Anderson and his son became a casualty of his "house cleaning" when Bischoff fired Bryant while he was training at the WCW Power Plant.[5] This prompted Anderson to call Smoky Mountain Wrestling head Jim Cornette to try to get his son a job. Anderson's decision to deal with Cornette, someone Bischoff was on bad terms with, on WCW property, was the factor that led to his firing. Bischoff fired Anderson over the phone, even though he spoke to Anderson face-to-face the day before. The chain of events was covered in a "shoot" interview by Cornette. In his book, Controversy Creates Ca$h, Bischoff noted that Blackjack Mulligan once overheard Anderson trash-talking Bischoff to other WCW staff. Mulligan, who was loyal to Bischoff for giving him a job when he needed the money, promptly thumped Anderson.

Since that time, he has stayed away from the business, but wrote a book on it titled Inside Out.[6] He has also hinted at having heat with former partner and friend Ric Flair by criticizing that Flair has wrestled the same match for years. In his WWE Bio Ric Flair stated that after he left the WWE via a loser leaves town match with Mr. Perfect, that Ole who was running WCW asked him what good he was to WCW after he lost to Mr. Perfect on national TV. Flair took this as a personal attack and lead to him ending their friendship.[7] In July 2007, Gerweck.net reported that Anderson has been suffering from multiple sclerosis and had gotten worse with decreased mobility and memory loss. Anderson has also been vocal about his personal issues with Vince McMahon, Michael Hayes, Paul Heyman, Eric Bischoff, Tully Blanchard, Bruiser Brody and Lex Luger.

On February 27, 2011, it was announced that Ole Anderson had been nursing broken ribs due to a fall he suffered from earlier that day, as well as a broken arm.[8]